![[ComicBook/IronMan Comics]]:
* A few in the infamous ''Demon in a Bottle'' story, such as Tony desperately admitting to Bethany that he needs help.
** Not to mention Tony's armor malfunctioning due to sabotage and killing the foreign ambassador, who, up to that point, was {{Squee}}ing over the chance to actually meet his hero, Iron Man.
* Tony and Pepper [[spoiler: when having to make the decision to unplug Happy's life support after he falls into a vegetative coma fighting off Spymaster.]]
* Maria Hill's backstory, as revealed in Invincible Iron Man. Her mother died either during or shortly after her birth, her father hated her for it, and she grew up with everyone telling her that she was terrible, from her childhood, to being kicked out of high school, to when she was in the Marines, to when Fury was yelling at her. On top of this, she's shown being treated badly by the SHIELD agents around her, with one saying "so long, sweet cheeks" and her narration says that she can't resist slapping back once more. Is it any surprise that Maria's first instinct is usually to attack people?
** Even worse--we see a photograph of Maria's desk when she's clearing it out - it's of her shaking Fury's hand. This implies that she used to look up to Fury, but in another issue where he broke into the Helicarrier to warn her about the Skrulls, he didn't even remember meeting her before.

![[Anime/IronMan Marvel Anime: Iron Man]]
* Tony discovering [[spoiler:Yinsen is alive, but has gone completely insane.]]
** It makes [[spoiler:Yinsen's ''second'' death all the more heartwrenching]].

![[Film/IronMan Films]]
* TearJerker/IronMan1
* TearJerker/IronMan2
* TearJerker/IronMan3